HCID 54275688, compound → HCID 54183176, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.55 mL n-butyllithium in diethyl ether is cooled to -78° C. under a nitrogen atmosphere. To this cooled solution is added a solution of N-(4-fluorobenzoyl)-3-bromo-5-aminobenzothiophene (0.90 eq.) in diethyl ether. The reaction mixture is stirred at -78° C. for 1 hour and then to it is added dropwise a solution of 7-indolizinone (1.08 eq.) in diethyl ether. The reaction is stirred an additional 2 hours at -78° C. and is then gradually warmed to -20° C. over 55 minutes. The reaction mixture is then quenched with saturated aqueous sodium bicarbonate, diluted with additional diethyl ether and the phases separated. The organic phase is washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue is taken up in aqueous potassium hydroxide (10% in water) and heated to reflux for 15 hours. The mixture is concentrated in vacuo and the residue is subjected to flash silica gel chromatography. Fractions shown to contain product are combined and then concentrated under reduced pressure to give the title compound.

Provenance & Evidence